CN1279031C - 具有除草活性的旋光(r)－苯氧基丙酸－n－甲基－n－2－氟苯基酰胺化合物 - Google Patents
具有除草活性的旋光(r)－苯氧基丙酸－n－甲基－n－2－氟苯基酰胺化合物 Download PDFInfo
- Publication number
- CN1279031C CN1279031C CN01823753.3A CN01823753A CN1279031C CN 1279031 C CN1279031 C CN 1279031C CN 01823753 A CN01823753 A CN 01823753A CN 1279031 C CN1279031 C CN 1279031C
- Authority
- CN
- China
- Prior art keywords
- hydrogen
- alkyl
- compound
- methyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 6
- XJKUFNKIQNIROK-GFCCVEGCSA-N (2r)-n-(2-fluorophenyl)-n-methyl-2-phenoxypropanamide Chemical class O([C@H](C)C(=O)N(C)C=1C(=CC=CC=1)F)C1=CC=CC=C1 XJKUFNKIQNIROK-GFCCVEGCSA-N 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 230000000694 effects Effects 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 40
- 244000025254 Cannabis sativa Species 0.000 claims description 21
- 235000007164 Oryza sativa Nutrition 0.000 claims description 19
- 241000192043 Echinochloa Species 0.000 claims description 18
- 235000009566 rice Nutrition 0.000 claims description 18
- 238000009333 weeding Methods 0.000 claims description 13
- 230000012010 growth Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 241000209094 Oryza Species 0.000 claims 3
- 239000000463 material Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 abstract description 15
- 229910052736 halogen Inorganic materials 0.000 abstract description 15
- 150000002367 halogens Chemical group 0.000 abstract description 15
- 125000000217 alkyl group Chemical group 0.000 abstract description 14
- 229910052731 fluorine Chemical group 0.000 abstract description 8
- 239000011737 fluorine Chemical group 0.000 abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 7
- 241000196324 Embryophyta Species 0.000 abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 abstract description 7
- 230000003287 optical effect Effects 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000002585 base Substances 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 240000007594 Oryza sativa Species 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- -1 sulphinyl Chemical group 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000003810 ethyl acetate extraction Methods 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- LZRGSWJIJWYPAU-UHFFFAOYSA-N FC1=C(C=CC=C1)N(C(=O)NN=O)C.C(CC)(=O)O Chemical compound FC1=C(C=CC=C1)N(C(=O)NN=O)C.C(CC)(=O)O LZRGSWJIJWYPAU-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- GLFNRNCRTAAWOR-WNQIDUERSA-N FC1=C(C=CC=C1)N(C(=O)NN=O)C.Br[C@H](C(=O)O)C Chemical compound FC1=C(C=CC=C1)N(C(=O)NN=O)C.Br[C@H](C(=O)O)C GLFNRNCRTAAWOR-WNQIDUERSA-N 0.000 description 2
- KHBXGOJNTXKGAI-FYZOBXCZSA-N FC1=C(C=CC=C1)N(C(=O)NN=O)C.OC1=CC=C(O[C@@H](C(=O)O)C)C=C1 Chemical compound FC1=C(C=CC=C1)N(C(=O)NN=O)C.OC1=CC=C(O[C@@H](C(=O)O)C)C=C1 KHBXGOJNTXKGAI-FYZOBXCZSA-N 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 2
- MONMFXREYOKQTI-REOHCLBHSA-N (2s)-2-bromopropanoic acid Chemical compound C[C@H](Br)C(O)=O MONMFXREYOKQTI-REOHCLBHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LVVQTPZQNHQLOM-UHFFFAOYSA-N 2,6-dichloro-1,3-benzoxazole Chemical compound C1=C(Cl)C=C2OC(Cl)=NC2=C1 LVVQTPZQNHQLOM-UHFFFAOYSA-N 0.000 description 1
- FYRGAOZTXCHMGK-UHFFFAOYSA-N 2,6-difluoro-n-methylaniline Chemical compound CNC1=C(F)C=CC=C1F FYRGAOZTXCHMGK-UHFFFAOYSA-N 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- LDVAIJZDACHGML-UHFFFAOYSA-N 2-fluoro-n-methylaniline Chemical compound CNC1=CC=CC=C1F LDVAIJZDACHGML-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ANCDHBXLDURTHN-UHFFFAOYSA-N 2-phenoxypropanamide Chemical class NC(=O)C(C)OC1=CC=CC=C1 ANCDHBXLDURTHN-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000003666 Amidosulfuron Substances 0.000 description 1
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 1
- 239000005469 Azimsulfuron Substances 0.000 description 1
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 239000005484 Bifenox Substances 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000269333 Caudata Species 0.000 description 1
- 239000005502 Cyhalofop-butyl Substances 0.000 description 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 239000005584 Metsulfuron-methyl Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 244000046109 Sorghum vulgare var. nervosum Species 0.000 description 1
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- PWAJCNITSBZRBL-UHFFFAOYSA-N ketazolam Chemical compound O1C(C)=CC(=O)N2CC(=O)N(C)C3=CC=C(Cl)C=C3C21C1=CC=CC=C1 PWAJCNITSBZRBL-UHFFFAOYSA-N 0.000 description 1
- 229960004423 ketazolam Drugs 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- XJKUFNKIQNIROK-UHFFFAOYSA-N n-(2-fluorophenyl)-n-methyl-2-phenoxypropanamide Chemical class C=1C=CC=C(F)C=1N(C)C(=O)C(C)OC1=CC=CC=C1 XJKUFNKIQNIROK-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- SEGKEOBRCVZLKT-UHFFFAOYSA-N propanoic acid thionyl dichloride Chemical compound C(CC)(=O)O.S(=O)(Cl)Cl SEGKEOBRCVZLKT-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2001/001845 WO2003037085A1 (en) | 2001-11-01 | 2001-11-01 | Optically active herbicidal (r)-phenoxypropionic acid-n-methyl-n-2-fluorophenyl amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1558717A CN1558717A (zh) | 2004-12-29 |
| CN1279031C true CN1279031C (zh) | 2006-10-11 |
Family
ID=19198468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN01823753.3A Ceased CN1279031C (zh) | 2001-11-01 | 2001-11-01 | 具有除草活性的旋光(r)－苯氧基丙酸－n－甲基－n－2－氟苯基酰胺化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20050043180A1 (pt) |
| EP (1) | EP1448058A4 (pt) |
| JP (1) | JP2005507402A (pt) |
| CN (1) | CN1279031C (pt) |
| AU (1) | AU2002212806B2 (pt) |
| BG (1) | BG66413B1 (pt) |
| BR (1) | BRPI0117166B1 (pt) |
| CA (1) | CA2465342C (pt) |
| HU (1) | HU230485B1 (pt) |
| WO (1) | WO2003037085A1 (pt) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100884933B1 (ko) * | 2007-07-03 | 2009-02-23 | 주식회사경농 | 광활성 (ｒ)-알릴옥시프로피온산 아마이드 화합물 및 이를포함하는 제초제 조성물 |
| US8097712B2 (en) | 2007-11-07 | 2012-01-17 | Beelogics Inc. | Compositions for conferring tolerance to viral disease in social insects, and the use thereof |
| US8962584B2 (en) | 2009-10-14 | 2015-02-24 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Compositions for controlling Varroa mites in bees |
| EA029482B1 (ru) | 2010-03-08 | 2018-04-30 | Монсанто Текнолоджи Ллс | Молекулы полинуклеотидов для регуляции генов у растений |
| CN101822262A (zh) * | 2010-05-18 | 2010-09-08 | 东莞市瑞德丰生物科技有限公司 | 一种除草组合物 |
| BR112014005954A2 (pt) | 2011-09-13 | 2020-12-01 | Monsanto Technology Llc | métodos e composições químicas agrícolas para controle de planta, método de redução de expressão de um gene dhps em uma planta, cassete de expressão microbiana, método para fazer um polinucleotídeo, método de identificação de polinucleotídeos úteis na modulação de expressão do gene dhps |
| MX350771B (es) | 2011-09-13 | 2017-09-15 | Monsanto Technology Llc | Métodos y composiciones para el control de malezas. |
| CA2848685A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control comprising topical application of a glutamine synthetase polynucleotide |
| US10806146B2 (en) | 2011-09-13 | 2020-10-20 | Monsanto Technology Llc | Methods and compositions for weed control |
| US10760086B2 (en) | 2011-09-13 | 2020-09-01 | Monsanto Technology Llc | Methods and compositions for weed control |
| AR088155A1 (es) | 2011-09-13 | 2014-05-14 | Monsanto Technology Llc | Metodos y composiciones para el control de malezas |
| CA2848680C (en) | 2011-09-13 | 2020-05-19 | Monsanto Technology Llc | Methods and compositions for weed control |
| EP2756083B1 (en) | 2011-09-13 | 2020-08-19 | Monsanto Technology LLC | Methods and compositions for weed control |
| US10829828B2 (en) | 2011-09-13 | 2020-11-10 | Monsanto Technology Llc | Methods and compositions for weed control |
| UY34822A (es) | 2012-05-24 | 2013-12-31 | Seeds Ltd Ab | Composiciones y métodos para silenciar la expresión genética |
| US10683505B2 (en) | 2013-01-01 | 2020-06-16 | Monsanto Technology Llc | Methods of introducing dsRNA to plant seeds for modulating gene expression |
| CN105358695B (zh) | 2013-01-01 | 2019-07-12 | A.B.种子有限公司 | 将dsRNA引入植物种子以调节基因表达的方法 |
| CN105263329B (zh) | 2013-03-13 | 2020-09-18 | 孟山都技术公司 | 用于杂草控制的方法和组合物 |
| CN105074008A (zh) | 2013-03-13 | 2015-11-18 | 孟山都技术有限公司 | 用于杂草控制的方法和组合物 |
| US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| BR112016000555B1 (pt) | 2013-07-19 | 2022-12-27 | Monsanto Technology Llc | Método para controlar uma infestação da espécie de leptinotarsa em uma planta, composição inseticida e construção de dna recombinante |
| US9850496B2 (en) | 2013-07-19 | 2017-12-26 | Monsanto Technology Llc | Compositions and methods for controlling Leptinotarsa |
| BR112016009963A2 (pt) | 2013-11-04 | 2017-12-05 | Beeologics Inc | composições e métodos para controlar artrópodes parasitas e infestações por praga |
| UA119253C2 (uk) | 2013-12-10 | 2019-05-27 | Біолоджикс, Інк. | Спосіб боротьби із вірусом у кліща varroa та у бджіл |
| CN105979770B (zh) | 2014-01-15 | 2019-07-05 | 孟山都技术公司 | 用于使用epsps多核苷酸的杂草控制的方法和组合物 |
| BR112016022711A2 (pt) | 2014-04-01 | 2017-10-31 | Monsanto Technology Llc | composições e métodos para controle de pragas de inseto |
| CA2953347A1 (en) | 2014-06-23 | 2015-12-30 | Monsanto Technology Llc | Compositions and methods for regulating gene expression via rna interference |
| US11807857B2 (en) | 2014-06-25 | 2023-11-07 | Monsanto Technology Llc | Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression |
| CA2955842A1 (en) | 2014-07-29 | 2016-02-04 | Monsanto Technology Llc | Compositions and methods for controlling insect pests |
| UA124255C2 (uk) | 2015-01-22 | 2021-08-18 | Монсанто Текнолоджі Елелсі | Інсектицидна композиція та спосіб боротьби з leptinotarsa |
| CN107750125A (zh) | 2015-06-02 | 2018-03-02 | 孟山都技术有限公司 | 用于将多核苷酸递送至植物中的组合物和方法 |
| US10655136B2 (en) | 2015-06-03 | 2020-05-19 | Monsanto Technology Llc | Methods and compositions for introducing nucleic acids into plants |
| CN105820134A (zh) * | 2016-03-24 | 2016-08-03 | 山东海诺格生物科技有限公司 | 一种具有除草活性的化合物及其制备方法和应用 |
| CN110863020B (zh) * | 2019-12-19 | 2022-12-23 | 湖南速博生物技术有限公司 | 一种酶法合成噁唑酰草胺的方法 |
| CN112314610A (zh) * | 2020-10-28 | 2021-02-05 | 安徽润农腾辉生物科技有限公司 | 一种包含噁唑酰草胺、氯吡嘧磺隆和丁草胺的除草组合物 |
| CN113068703A (zh) * | 2021-04-09 | 2021-07-06 | 安徽海日农业发展有限公司 | 一种基于噁唑酰草胺和丁草胺的水稻用复合除草剂 |
| CN113717123B (zh) * | 2021-09-10 | 2023-10-10 | 内蒙古蓝科生物科技有限公司 | 一种恶唑酰草胺的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5254527A (en) * | 1977-12-24 | 1993-10-19 | Hoechst Aktiengesellschaft | Optically active herbicidal ethyl-2-(4-(6-chloro-benzoxazol-2-yloxy)-phenoxy)-propionate |
| JPH0211580A (ja) * | 1988-06-30 | 1990-01-16 | Kumiai Chem Ind Co Ltd | フェノキシプロピオン酸アミド誘導体及び除草剤 |
| CA2216764A1 (en) * | 1996-10-11 | 1998-04-11 | Samuel Eugene Sherba | Phenylamides as marine antifouling agents |
| US6600048B2 (en) * | 1998-07-25 | 2003-07-29 | Dongbu Hannong Chemical Co., Ltd. | Herbicidal phenoxypropionic acid N-alkyl-N-2-fluorophenyl amide compounds |
| KR100314776B1 (ko) * | 1998-07-25 | 2001-11-17 | 우종일 | 제초성 페녹시프로피온산 ｎ-알킬-ｎ-2-플루오로페닐 아미드화합물 |
| JP3889967B2 (ja) * | 1999-08-03 | 2007-03-07 | ドンブ ハンノン ケミカル カンパニー リミテッド | 高選択性除草剤フェノキシプロピオン酸アルコキシカルボニルアニリド化合物及びその製造方法 |
-
2001
- 2001-11-01 CA CA002465342A patent/CA2465342C/en not_active Expired - Fee Related
- 2001-11-01 AU AU2002212806A patent/AU2002212806B2/en not_active Expired
- 2001-11-01 US US10/494,084 patent/US20050043180A1/en not_active Abandoned
- 2001-11-01 WO PCT/KR2001/001845 patent/WO2003037085A1/en active Application Filing
- 2001-11-01 BR BRPI0117166-6A patent/BRPI0117166B1/pt active IP Right Grant
- 2001-11-01 JP JP2003539442A patent/JP2005507402A/ja active Pending
- 2001-11-01 CN CN01823753.3A patent/CN1279031C/zh not_active Ceased
- 2001-11-01 HU HU0402057A patent/HU230485B1/hu not_active IP Right Cessation
- 2001-11-01 EP EP01981146A patent/EP1448058A4/en not_active Withdrawn
-
2004
- 2004-04-26 BG BG108697A patent/BG66413B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2465342C (en) | 2009-09-08 |
| HU230485B1 (hu) | 2016-08-29 |
| CA2465342A1 (en) | 2003-05-08 |
| JP2005507402A (ja) | 2005-03-17 |
| BG66413B1 (bg) | 2014-02-28 |
| EP1448058A4 (en) | 2005-01-26 |
| BR0117166A (pt) | 2004-10-26 |
| US20050043180A1 (en) | 2005-02-24 |
| HUP0402057A2 (hu) | 2005-01-28 |
| BG108697A (en) | 2005-03-31 |
| AU2002212806B2 (en) | 2006-06-08 |
| BRPI0117166B1 (pt) | 2015-04-22 |
| CN1558717A (zh) | 2004-12-29 |
| WO2003037085A1 (en) | 2003-05-08 |
| EP1448058A1 (en) | 2004-08-25 |
| HUP0402057A3 (en) | 2005-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1279031C (zh) | 具有除草活性的旋光(r)－苯氧基丙酸－n－甲基－n－2－氟苯基酰胺化合物 | |
| CN1141876C (zh) | 具有除草活性的苯氧基丙酸n-烷基-n-2-氟苯基酰胺化合物 | |
| CN1045958C (zh) | 四唑啉酮类化合物及其制备方法、含其的除草组合物和其作为除草剂的用途 | |
| CN1035752A (zh) | 基于吡唑羧酸衍生物的植物防护剂 | |
| CN1069268A (zh) | 新型除草剂 | |
| AU2002212806A1 (en) | Optically active herbicidal (R)-phenoxypropionic acid-N-methyl-N-2-fluorophenyl amides | |
| CN1066843A (zh) | 除草剂 | |
| CN1172931C (zh) | 有除草剂活性的吡啶磺酰脲衍生物 | |
| CN1046900A (zh) | 用作杀虫剂和植物生长调节剂的杂环二酮 | |
| CN1036571A (zh) | 苯并恶嗪酮化合物和含有这种化合物的除草组合物 | |
| CN1303081C (zh) | 除草的5－苄氧基甲基－1,2－异噁唑啉衍生物 | |
| CN86104887A (zh) | (r)-2-[4-(5-氯-3-氟吡啶-2-基氧)苯氧基]丙酸炔丙基酯的制备方法及其作为除草剂的应用 | |
| CN1058395A (zh) | 芳氨基羰基化合物 | |
| CN1060385A (zh) | 除草剂 | |
| CN88100210A (zh) | 四唑啉酮除草剂 | |
| CN1058491C (zh) | 具有除草活性的四唑啉酮类化合物 | |
| CN86103235A (zh) | 邻甲氧甲酰磺酰脲类除草剂 | |
| CN1022455C (zh) | 新的除草剂组合物 | |
| CN1040437C (zh) | 除草的喹啉基噁二唑衍生物,它们的制备方法和含有它们的除草组合物 | |
| CN100334949C (zh) | 高选择性除草用苯氧基丙酸烷氧基羰基n－酰苯胺化合物及其制备方法 | |
| CN1019941C (zh) | 用苯并异噻唑生物防治稻瘟病的方法 | |
| CN1279235A (zh) | 1－环丙基四唑啉酮 | |
| CN1038012C (zh) | 含有取代的吡啶磺酰胺化合物或其盐的除草剂 | |
| CN86106552A (zh) | N-苯磺酰基异烟酰胺衍生物和它们作为杀真菌剂和杀菌剂的用途 | |
| CN1039713C (zh) | 3－氯杂双环[3.1.0]己烷－2－酮衍生物和含有它们作为除草活性成分的除草组合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: DONGBU FARM HANNONG CO., LTD. Free format text: FORMER OWNER: DONGBU HITEK CO,. LTD. Effective date: 20130110 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| C56 | Change in the name or address of the patentee |
Owner name: DONGBU HITEK CO,. LTD. Free format text: FORMER NAME: HANWHA CORP. |
|
| CP01 | Change in the name or title of a patent holder |
Address after: Seoul, South Kerean Patentee after: Dong Buhitek(zhu) Address before: Seoul, South Kerean Patentee before: DONGBU HANNONG CHEMICAL CO.,LTD. |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20130110 Address after: Seoul, South Kerean Patentee after: Mama Han Nong (strain) east Fu Address before: Seoul, South Kerean Patentee before: Dong Buhitek(zhu) |
|
| CP01 | Change in the name or title of a patent holder |
Address after: Seoul, South Kerean Patentee after: Han Nong, fu'amu Address before: Seoul, South Kerean Patentee before: Mama Han Nong (strain) east Fu |
|
| CP01 | Change in the name or title of a patent holder | ||
| IW01 | Full invalidation of patent right |
Decision date of declaring invalidation: 20190730 Decision number of declaring invalidation: 41175 Granted publication date: 20061011 |
|
| IW01 | Full invalidation of patent right |